Product Name

  • Name

    (5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione

  • EINECS 688-342-2
  • CAS No. 168828-82-8
  • Article Data26
  • CAS DataBase
  • Density 1.362 g/cm3
  • Solubility
  • Melting Point 110-112 °C
  • Formula C14H17FN2O4
  • Boiling Point 494.241 °C at 760 mmHg
  • Molecular Weight 296.298
  • Flash Point 252.708 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 168828-82-8 ((5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione)
  • Hazard Symbols
  • Synonyms 2-Oxazolidinone,3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-(hydroxymethyl)-, (R)-;S-5-Azidomethyl-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone;(5R)-3-[3-Fluoro-4-(morpholin-4-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one;CHEMBL596913;AC-4277;TL8001308;
  • PSA 62.24000
  • LogP 1.10980

Synthetic route

((S)-2,3-Dihydroxy-propyl)-(3-fluoro-4-morpholin-4-yl-phenyl)-carbamic acid benzyl ester
912552-56-8

((S)-2,3-Dihydroxy-propyl)-(3-fluoro-4-morpholin-4-yl-phenyl)-carbamic acid benzyl ester

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃;96%
(R)-glycidyl butyrate
60456-26-0

(R)-glycidyl butyrate

benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate
168828-81-7, 1027135-00-7

benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Stage #1: benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water		85.1%
Stage #1: benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate With n-butyllithium; butan-1-ol In tetrahydrofuran; hexane at -15 - 30℃; Inert atmosphere;
Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -10 - 15℃;
Stage #3: With water In tetrahydrofuran; hexane; ethyl acetate		85%
Stage #1: benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.63333h;
Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃; for 22.1h;		83%
carbon dioxide
124-38-9

carbon dioxide

(S)-N-(2,3-epoxy-1-propyl)-3-fluoro-4-(4-morpholinyl)aniline

(S)-N-(2,3-epoxy-1-propyl)-3-fluoro-4-(4-morpholinyl)aniline

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
With dmap; C20H14AlNO3 In dichloromethane at 25℃; under 760.051 Torr; for 60h; Sealed tube; stereoselective reaction;85%
N-ethoxycarbonyl-3-fluoro-4-morpholinyl aniline
565176-83-2

N-ethoxycarbonyl-3-fluoro-4-morpholinyl aniline

(R)-glycidyl butyrate
60456-26-0

(R)-glycidyl butyrate

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Stage #1: N-ethoxycarbonyl-3-fluoro-4-morpholinyl aniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3.5h; Inert atmosphere;
Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water at 20℃; for 0.5h; Product distribution / selectivity;		80%
N-[4(R)-(2,2-dimethyl-1,3-dioxolane-4-yl)methyl]-3-fluoro-4-morpholinylaniline
903593-93-1

N-[4(R)-(2,2-dimethyl-1,3-dioxolane-4-yl)methyl]-3-fluoro-4-morpholinylaniline

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Stage #1: N-[4(R)-(2,2-dimethyl-1,3-dioxolane-4-yl)methyl]-3-fluoro-4-morpholinylaniline With hydrogenchloride; water In methanol at 20℃; for 8h;
Stage #2: bis(trichloromethyl) carbonate With sodium carbonate at 20℃; for 24h; Further stages.;		56%
(5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-carbaldehyde-2-oxazolidinone

(5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-carbaldehyde-2-oxazolidinone

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; Yield given;
(R)-glycidyl butyrate
60456-26-0

(R)-glycidyl butyrate

3-fluoro-4-(morpholinyl)aniline
93246-53-8

3-fluoro-4-(morpholinyl)aniline

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multistep reaction;
3-(3-fluoro-4-morpholin-4-yl-phenylamino)-propan-1-ol

3-(3-fluoro-4-morpholin-4-yl-phenylamino)-propan-1-ol

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: aq. NaHCO3 / acetone
2.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C
3.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C
3.2: NaBH4 / methanol
3.3: 86 percent / CuSO4 / methanol
4.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C
View Scheme
(3-fluoro-4-morpholin-4-yl-phenyl)-(3-oxo-propyl)-carbamic acid benzyl ester
912552-55-7

(3-fluoro-4-morpholin-4-yl-phenyl)-(3-oxo-propyl)-carbamic acid benzyl ester

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C
1.2: NaBH4 / methanol
1.3: 86 percent / CuSO4 / methanol
2.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C
View Scheme
(3-fluoro-4-morpholin-4-yl-phenyl)-(3-hydroxy-propyl)-carbamic acid benzyl ester
912552-54-6

(3-fluoro-4-morpholin-4-yl-phenyl)-(3-hydroxy-propyl)-carbamic acid benzyl ester

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C
2.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C
2.2: NaBH4 / methanol
2.3: 86 percent / CuSO4 / methanol
3.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C
View Scheme
3-fluoro-4-(morpholinyl)aniline
93246-53-8

3-fluoro-4-(morpholinyl)aniline

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: NaI; Na2CO3 / dimethylformamide / 65 °C
2.1: aq. NaHCO3 / acetone
3.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C
4.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C
4.2: NaBH4 / methanol
4.3: 86 percent / CuSO4 / methanol
5.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C
View Scheme
Multi-step reaction with 2 steps
1.1: NaHCO3
2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
2.2: hexane; tetrahydrofuran / -78 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 70 percent / sodium bicarbonate / acetone; H2O
2: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 35 min, 2.) THF, hexane, -78 deg C, 1 h
View Scheme
3,4-difluoronitrobenzene
369-34-6

3,4-difluoronitrobenzene

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N,N-diisopropylethylamine
2.1: ammonium formate / 10 percent Pd/C / methanol; tetrahydrofuran
3.1: NaHCO3
4.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
4.2: hexane; tetrahydrofuran / -78 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: N,N-diisopropylethylamine / acetonitrile / 17 h / Heating
2: H2 / PtO2 / methanol / 3 h / 20 °C / 1471.02 Torr
View Scheme
Multi-step reaction with 4 steps
1: 98 percent / N,N-diisopropylethylamine / ethyl acetate
2: ammonium formate / 10percent Pd/C
3: 70 percent / sodium bicarbonate / acetone; H2O
4: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 35 min, 2.) THF, hexane, -78 deg C, 1 h
View Scheme
3-fluoro-4-(4-morpholinyl)nitrobenzene
2689-39-6

3-fluoro-4-(4-morpholinyl)nitrobenzene

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: ammonium formate / 10 percent Pd/C / methanol; tetrahydrofuran
2.1: NaHCO3
3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
3.2: hexane; tetrahydrofuran / -78 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: H2 / PtO2 / methanol / 3 h / 20 °C / 1471.02 Torr
View Scheme
Multi-step reaction with 3 steps
1: ammonium formate / 10percent Pd/C
2: 70 percent / sodium bicarbonate / acetone; H2O
3: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 35 min, 2.) THF, hexane, -78 deg C, 1 h
View Scheme
(R)-2-(3-Fluoro-4-morpholin-4-yl-phenylamino)-1-{(4R,5R)-5-[(R)-2-(3-fluoro-4-morpholin-4-yl-phenylamino)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol
905945-96-2

(R)-2-(3-Fluoro-4-morpholin-4-yl-phenylamino)-1-{(4R,5R)-5-[(R)-2-(3-fluoro-4-morpholin-4-yl-phenylamino)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: CH2Cl2 / Ambient temperature
2: 2N HCl / Ambient temperature
3: lead tetraacetate (LTA) / tetrahydrofuran / 0 °C
4: NaBH4 / methanol / 0 °C
View Scheme
C28H32F2N4O8
239438-43-8

C28H32F2N4O8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lead tetraacetate (LTA) / tetrahydrofuran / 0 °C
2: NaBH4 / methanol / 0 °C
View Scheme
C31H36F2N4O8
239438-39-2

C31H36F2N4O8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2N HCl / Ambient temperature
2: lead tetraacetate (LTA) / tetrahydrofuran / 0 °C
3: NaBH4 / methanol / 0 °C
View Scheme
N-[3-chloro-2-(R)-hydroxypropyl]-3-fluoro-4-(morpholin-4-yl)aniline
868405-66-7

N-[3-chloro-2-(R)-hydroxypropyl]-3-fluoro-4-(morpholin-4-yl)aniline

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1,1'-carbonyldiimidazole / dichloromethane / 24 h / 20 - 30 °C
2: N,N-dimethyl-formamide / 120 °C
3: water; sodium t-butanolate / tetrahydrofuran / 0.5 h / 0 - 15 °C
View Scheme
Multi-step reaction with 3 steps
1: dichloromethane / 24 h / 25 - 30 °C
2: N,N-dimethyl-formamide / 120 °C
3: sodium t-butanolate; water / tetrahydrofuran / 0.5 h / 0 - 15 °C
View Scheme
(5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone

(5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 120 °C
2: water; sodium t-butanolate / tetrahydrofuran / 0.5 h / 0 - 15 °C
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 120 °C
2: sodium t-butanolate; water / tetrahydrofuran / 0.5 h / 0 - 15 °C
View Scheme
(R)-(3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl acetate
496031-56-2

(R)-(3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl acetate

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
With water; sodium t-butanolate In tetrahydrofuran at 0 - 15℃; for 0.5h;
With water; sodium t-butanolate In tetrahydrofuran at 0 - 15℃; for 0.5h;50 g
(S)-3-chloropropan-1,2-diol
60827-45-4

(S)-3-chloropropan-1,2-diol

benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate
168828-81-7, 1027135-00-7

benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
With potassium tert-butylate; lithium diisopropyl amide
(2R)-1-chloro-3-{[3-fluoro-4-(morpholin-4-yl)phenyl]amino}-propan-2-ol

(2R)-1-chloro-3-{[3-fluoro-4-(morpholin-4-yl)phenyl]amino}-propan-2-ol

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / dichloromethane; water / 24 h
2: dmap; C20H14AlNO3 / dichloromethane / 60 h / 25 °C / 760.05 Torr / Sealed tube
View Scheme
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-methyl methanesulfonate
174649-09-3

(R)-methyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 0.5h;100%
With triethylamine In tetrahydrofuran at 8 - 15℃; for 3.75h; Cooling with ice; Inert atmosphere;96%
With triethylamine In dichloromethane at 20 - 30℃;95%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-[N-3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl 4-methylbenzenesulfonate
168828-83-9

(R)-[N-3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;92%
With triethylamine In dichloromethane at 0 - 20℃; for 18.8333h;92%
With triethylamine In dichloromethane at 0 - 20℃; for 18h;85%
4-iodobenzenesulfonyl chloride
98-61-3

4-iodobenzenesulfonyl chloride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-iodobenzenesulfonate

(R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-iodobenzenesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 18h;82.5%
4-bromobenzenesulfonyl chloride
98-58-8

4-bromobenzenesulfonyl chloride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-bromobenzenesulfonate

(R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-bromobenzenesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 26h;81.5%
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

thioacetic acid
507-09-5

thioacetic acid

linezolid
165800-03-3

linezolid

Conditions
ConditionsYield
Stage #1: (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol With methanesulfonyl chloride
Stage #2: With sodium azide
Stage #3: tiolacetic acid stereoselective reaction;		81%
4-Fluorobenzenesulfonyl chloride
349-88-2

4-Fluorobenzenesulfonyl chloride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-fluorobenzenesulfonate

(R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-fluorobenzenesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 18h;80.3%
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-5-azidomethyl-3-(3-fluoro-4-(morpholin-4-yl)phenyl)oxazolidin-2-one
168828-84-0

(R)-5-azidomethyl-3-(3-fluoro-4-(morpholin-4-yl)phenyl)oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃;
Stage #2: With sodium azide In N,N-dimethyl-formamide at 80℃; Further stages.;		79%
Multi-step reaction with 2 steps
1: Et3N / CH2Cl2 / 4 h / 0 °C
2: NaN3 / dimethylformamide / 75 °C
View Scheme
Multi-step reaction with 2 steps
1: Et3N / tetrahydrofuran / 2 h / 20 °C
2: sodium azide / dimethylformamide / 6 h / 65 °C
View Scheme
acetic anhydride
108-24-7

acetic anhydride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-(3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl acetate
496031-56-2

(R)-(3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl acetate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 20℃; for 4h;75%
isoxazol-3-ol
5777-20-8

isoxazol-3-ol

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

5(R)-Isoxazol-3-yloxymethyl-3-(4-morpholino-3-fluoro-phenyl)oxazolidin-2-one
252260-22-3

5(R)-Isoxazol-3-yloxymethyl-3-(4-morpholino-3-fluoro-phenyl)oxazolidin-2-one

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran69%
...Expand
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

4-Nitro-benzenesulfonic acid (R)-3-(3-fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester
198410-26-3

4-Nitro-benzenesulfonic acid (R)-3-(3-fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester

Conditions
ConditionsYield
With triethylamine
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine
168828-90-8

(S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N / CH2Cl2 / 4 h / 0 °C
2: NaN3 / dimethylformamide / 75 °C
3: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr
View Scheme
Multi-step reaction with 2 steps
1: Et3N
2: NH3 / methanol
View Scheme
Multi-step reaction with 3 steps
1: Et3N / tetrahydrofuran / 2 h / 20 °C
2: sodium azide / dimethylformamide / 6 h / 65 °C
3: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C
View Scheme
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

linezolid
165800-03-3

linezolid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Et3N / CH2Cl2 / 4 h / 0 °C
2: NaN3 / dimethylformamide / 75 °C
3: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr
4: pyridine
View Scheme
Multi-step reaction with 3 steps
1: Et3N
2: NH3 / methanol
3: 2 h / 40 °C
View Scheme
Multi-step reaction with 3 steps
1: Et3N
2: NaN3 / dimethylsulfoxide / 80 °C
3: 86 percent / Ambient temperature
View Scheme
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-[{N-3-(3-fluoro-4-morpholinophenyl)-2-oxo-oxazolidin-5-yl}methyl]isothiocyanate
216869-07-7

(R)-[{N-3-(3-fluoro-4-morpholinophenyl)-2-oxo-oxazolidin-5-yl}methyl]isothiocyanate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: Et3N / tetrahydrofuran / 2 h / 20 °C
2.1: sodium azide / dimethylformamide / 6 h / 65 °C
3.1: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C
4.1: Et3N / tetrahydrofuran / 4 h / 0 °C
4.2: ethyl chloroformate / tetrahydrofuran / 1 h / 0 °C
View Scheme
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(S)-N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]methyldithiocarbamate
216868-96-1

(S)-N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]methyldithiocarbamate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Et3N / tetrahydrofuran / 2 h / 20 °C
2: sodium azide / dimethylformamide / 6 h / 65 °C
3: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C
4: Et3N / tetrahydrofuran / 7 h / 0 °C
5: Et3N / tetrahydrofuran / 0.5 h / 20 °C
View Scheme
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(S)-N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thiourea

(S)-N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thiourea

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: Et3N / tetrahydrofuran / 2 h / 20 °C
2.1: sodium azide / dimethylformamide / 6 h / 65 °C
3.1: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C
4.1: Et3N / tetrahydrofuran / 4 h / 0 °C
4.2: ethyl chloroformate / tetrahydrofuran / 1 h / 0 °C
5.1: 40 percent / NH3 / methanol / 3 h / 0 °C
View Scheme
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

[(S)-3-(3-Fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-dithiocarbamic acid

[(S)-3-(3-Fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-dithiocarbamic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Et3N / tetrahydrofuran / 2 h / 20 °C
2: sodium azide / dimethylformamide / 6 h / 65 °C
3: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C
4: Et3N / tetrahydrofuran / 7 h / 0 °C
View Scheme

(5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione Specification

The (5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione with CAS registry number of 168828-82-8 is also known as 2-Oxazolidinone,3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-(hydroxymethyl)-, (5R)-. The IUPAC name is (5R)-3-(3-Fluoro-4-morpholin-4-ylphenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one. In addition, the formula is C14H17FN2O4 and the molecular weight is 296.29.

Physical properties about (5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidion are: (1)ACD/LogP: 0.59; (2)ACD/LogD (pH 7.4): 1; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 2; (5)ACD/KOC (pH 5.5): 19; (6)ACD/KOC (pH 7.4): 52; (7)#H bond acceptors: 6; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 4; (10)Index of Refraction: 1.572; (11)Molar Refractivity: 71.614 cm3; (12)Molar Volume: 217.595 cm3; (13)Surface Tension: 51.972 dyne/cm; (14)Density: 1.362 g/cm3; (15)Flash Point: 252.708 °C; (16)Enthalpy of Vaporization: 80.203 kJ/mol; (17)Boiling Point: 494.241 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1COCCN1C2=C(C=C(C=C2)N3CC(OC3=O)CO)F
2. Isomeric SMILES: C1COCCN1C2=C(C=C(C=C2)N3C[C@@H](OC3=O)CO)F
3. InChI: InChI=1S/C14H17FN2O4/c15-12-7-10(17-8-11(9-18)21-14(17)19)1-2-13(12)16-3-5-20-6-4-16/h1-2,7,11,18H,3-6,8-9H2/t11-/m1/s1
4. InChIKey: OLDRPBWULXUVTL-LLVKDONJSA-N

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